...even in a piece he did this fall for CRUISING WORLD, he suggests that only larger, fully-crewed boats head for Bermuda, and suggests a departure from either Norfolk or Beaufort for those that don't fit that category...
Of course, he formed most of his opinion before weather forecasting was as sophisticated as it is now, and the ability to retrieve weather info/routing while on passage was as commonplace as it is now... Back in his day, I think there was a pretty good argument for avoiding a route in the late fall that doesn't put you in the Gulf Stream until a few days out, as opposed to crossing the Stream quickly, as one can do from Hatteras/Beaufort... Also, pre-GPS, Bermuda used to be a very treacherous landfall, especially in heavy weather - now it no longer is, of course (grin)...
This recent storm that materialized from the remnants of Ida was a reminder of how uncertain calling the weather can be this time of the year. Up in this area at least, they didn't really call that one too far in advance... On the other hand, sounds like the the Caribbean 1500 had pretty much of a dream passage this year, the fleet held to the rhumb line all the way, and had moderate to strong winds on the beam for most of the trip...
If you're starting from Newport/New England, the temptation to do the Bermuda route is pretty strong, no question... A bunch of boats all left at the same time earlier this month, but sounds like they got hammered pretty good about halfway there... But I still think that, once given Dave was already in Beaufort, keeping Bermuda in the picture as a bailout definitely makes sense, but it could still turn out to be a pretty good slog to actually make it there, might be far more comfortable just to keep on going to the islands...